1
56
X. Zhang et al. / Tetrahedron Letters 51 (2010) 153–156
7
.
(a) Qiu, R.; Xu, X.; Li, Y.; Zhang, G.; Shao, L.; An, D.; Yin, S. Chem. Commun. 2009,
679; (b) Qiu, R.; Zhang, G.; Zhu, Y.; Xu, X.; Shao, L.; Li, Y.; An, D.; Yin, S. Chem.-
Eur. J. 2009, 15, 6488; (c) Qiu, R.; Zhu, Y.; Xu, X.; Li, Y.; Shao, L.; Ren, X.; Cai, X.;
An, D.; Yin, S. Catal. Commun. 2009, 10, 1889.
(a) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons:
New York, 1997; (b) Ramachandran, P. V.; Burghardt, T. E. Pure Appl. Chem.
was added for neutralization. After filtration, the aqueous layer was extracted
with Et
O (10 mL Â 3), and the organic layers were combined and washed with
brine, then dried with Na SO The resulted solution was subject to
1
2
2
4
.
evaporation, whereas the residue was subject to silica gel column
chromatograph (ethyl acetate/petroleum ether = 1/8). The collected colorless
oil showed an isolated yield of 142.0 mg, 96%. All aldehydes, acetophenone,
and tetraallyltin are commercially available. All homoallylic alcohols 2a–j have
been reported, and 1H NMR spectra data of the products are consistent with
our previous results (see Refs. 7a,b) and those of Jiang et al. and Zhao and Cai
(see Refs. 19a,b).
8
.
2
5
006, 78, 1397; (c) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39,
67; (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207; (e) Yanagisawa, A.;
Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356; (f)
Sabitha, G.; Padmaja, P.; Yadav, J. S. Helv. Chim. Acta 2008, 91, 2235.
(a) Marshall, J. A. Chem. Rev. 1996, 96, 31; (b) Minakata, S.; Komatsu, M. Chem.
Rev. 2009, 109, 711; (c) Nagarapu, L.; Paturi, G.; Apuri, S.; Bantu, R.;
Bhavanthula, R. Synth. Commun. 2009, 39, 355.
9
.
1-Phenyl-3-buten-1-ol (2a): 1H NMR (CDCl
3
, 400 MHz, TMS): d 2.01 (1H, br s),
2.49–2.58 (2H, m), 4.75 (1H, t, J = 5.42 Hz), 5.14–5.20 (2H, m), 5.82 (1H, m),
7.25–7.43 (5H, m).
1
1
0. Kwiatkowski, P.; Chaladaj, W.; Jurczak Tetrahedron 2006, 62, 5116.
1. (a) Cokley, T. M.; Marshall, R. L.; McCluskey, A.; Young, D. J. Tetrahedron Lett.
2-Methylhex-5-en-3-ol (2b): 1H NMR (CDCl
3
, 400 MHz, TMS): d 0.91 (6H, d,
J = 7.2 Hz), 2.12–2.17 (1H, m), 2.23–2.34 (2H, m), 3.30–3.42 (1H, m), 5.02 (2H,
d, J=7.8 Hz), 5.08 (1H, S), 5.89–6.02 (1H, m).
1
996, 37, 1905; (b) Cokley, T. M.; Harvey, P. J.; Marshall, R. L.; McCluskey, A.;
Young, D. J. J. Org. Chem. 1997, 62, 1961; (c) McCluskey, A. Green Chem. 1999,
1-(p-Chlorophenyl)-3-buten-1-ol (2c): 1H NMR (CDCl
3
, 400 MHz, TMS): d 2.16
1
2
67; (d) McCluskey, A.; Muderawan, I. W.; Muntari; Young, D. J. J. Org. Chem.
001, 66, 7811.
(1H, s), 2.41–2.50 (2H, m), 4.71 (1H, dd, J = 6.8 Hz), 5.13–5.17 (2H, m), 5.73–
5.80 (1H, m), 7.26–7.32 (4H, m).
1
1
2. (a) Gordon, C. M.; Ritchie, C. Green Chem. 2002, 4, 124; (b) Law, M. C.; Wong, K.-Y.;
Chan, T. H. Green Chem. 2002, 4, 161.
1-(p-Trifluoromethylphenyl)-3-buten-1-ol (2d): 1H NMR (CDCl
3
, 400 MHz, TMS):
d 2.21(1H, s), 2.57–2.43 (2H, m), 4.80 (1H, m), 5.18 (2H, m), 5.75–5.83 (1H, m),
7.47 (2H, d, J=8.2 Hz), 7.61 (2H, d, J =8.2 Hz).1-(4-Nitrophenyl)but-3-en-1-ol
3. Synthesis of compound 1:
dissolved in 90.0 mL THF, then a solution of AgBF
0.0 mL THF was added. After the mixture was stirred in the dark at room
temperature for 3 h, it was filtered. The filtrate mixed with 10.0 mL hexane was
refrigerated for 24 h, giving colorless crystals (2.74 g, 95.6%). Compound 1: 1
NMR (acetone-d , 400 MHz, TMS): d 1.19 (1H, td, J = 13.6 Hz), 1.33–1.44 (2H,
m), 1.54–1.63 (3H, m), 1.84 (2H, d, J = 11.2 Hz), 2.16 (2H, d, J = 12.0 Hz), 3.50
1H, t, J = 12.0 Hz), 4.67 (2H, d, J = 15.6 Hz), 5.02 (2H, d, J = 15.6 Hz), 7.42 (2H,
td, J = 7.6 Hz), 7.58 (2H, t, J = 7.6 Hz), 7.76 (2H, d, J = 7.6 Hz), and 8.09 (2H, d,
J = 7.2 Hz); 13C NMR (acetone-d
, 100 MHz): d 25.89, 26.16, 26.29, 32.03, 65.07,
C
6
2
H11N(CH C
H
6 4
2
) BiCl (2.61 g, 5.0 mmol) was
(0.97 g, 5.0 mmol) in
(2e): 1H NMR (CDCl
3
, 400 MHz, TMS): d 2.13 (1H, br), 2.42–2.49 (1H, m), 2.54–
4
6
2.60 (1H, m), 4.86–4.89 (1H, m), 5.17–5.22 (2H, m), 5.74–5.84 (1H, m), 7.54
(2H, d, J=8.8 Hz), 8.21 (2H, d, J=8.8 Hz).
H
1-(p-Methoxyphenyl)-3-buten-1-ol (2f): 1H NMR (CDCl
3
, 400 MHz, TMS): d 1.94
6
(1H, br s), 2.50 (2H, d, J = 6.6 Hz), 3.81 (3H, s), 4.69 (1H, t, J = 6.3 Hz), 5.11–5.18
(2H, m), 5.80 (1H, m), 6.89 (2H, d, J = 8.8 Hz), 7.27 (2H, d, J = 8.8 Hz).1-(p-
(
Methylphenyl)-3-buten-1-ol (2g): 1H NMR (CDCl
3
, 400 MHz, TMS): d 2.01 (1H,
br s), 2.33 (3H, s), 2.48–2.51 (2H, m), 4.69 (1H, t, J = 6.6 Hz), 5.11–5.17 (2H, m),
5.76–5.81 (1H, m), 7.14 (2H, d, J = 7.8 Hz), 7.24 (2H, d, J = 7.8 Hz).Undec-1-en-4-
6
1
9
ol (2h): 1H NMR (CDCl
67.75, 68.06, 129.28, 129.55, 131.58, 137.77, and 154.44; F NMR (acetone-d
376 MHz): À154.437(s); HRMS calcd for 35BBiF N: 657.3419, found:
657.3414; Crystallographic data for 1: C 11N(C CH BiBF 12, colorless
6
,
3
, 400 MHz, TMS): d 0.88 (3H, t, J=7.0 Hz), 1.28 (12H, br
s), 1.44–1.48 (2H, m), 1.84 (1H, s), 2.11–2.17 (1H, m, one proton of CH ), 2.27–
), 3.62–3.66 (1H, m), 5.11–5.15 (2H, m), 5.79–
C
26
H
4
2
6
H
6
H
4
2
)
2
ÁC
4 6
H
2.32 (1H, m, one proton of CH
5.87 (1H, m).
2
prism, formula weight 657.34, monoclinic, P2(1)/n, a = 10.9011(12), b = 16.0649
À3
1-Phenylpent-4-en-2-ol (2i): 1H NMR (CDCl
(
18), c = 14.2625 (15), V = 2457.3(5), Z = 4, Dcalcd = 1.777 g cm , Rint = 0.069,
3
, 400 MHz, TMS): d 1.83 (1H, s),
R
1
= 0.056, wR
4. (a) Shimada, S.; Yamazaki, O.; Tanaka, T. J. Organomet. Chem. 2004, 689, 3012;
b) Bao, M.; Hayashi, T.; Shimada, S. Organometallics 2007, 26, 1816.
2
= 0.135, GOF = 0.86, CCDC No. 746982.
2.20–2.26 (1H, m), 2.30–2.35 (1H, m), 2.72 (1H, dd, J = 13.6 Hz), 2.81 (1H, dd,
J = 4.0 Hz), 3.87 (2H, m), 5.13–5.18 (2H, m), 5.86 (1H, m), 7.21–7.26 (3H, m),
1
(
7.29–7.34 (2H, m).1-(Furan-2-yl)but-3-en-1-ol (2j): 1H NMR (CDCl
3
, 400 MHz,
1
1
5. Ooi, T.; Goto, R.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 10494.
6. Typical procedure for the allylation reaction: To a solution of 1 (0.04 mmol,
TMS): d 1.93–2.12 (1H, br), 2.61–2.66 (2H, m), 4.76 (1H, t, J = 6.1 Hz), 5.14–5.22
(2H, m), 5.74–5.84 (1H, m), 6.25 (1H, d, J = 2.6 Hz), 6.33 (1H, q, J = 2.6 Hz), 7.39
(1H, d, J = 1.5 Hz).
2
3 2
3.9 mg) in 2.0 mL solvent (CH OH/H O = 9:1), PhCHO (106.1 mg, 1 mmol),
and tetraallylstannane (0.3 mmol, 84.9 mg) were added. Then the mixture was
stirred at room temperature and subject to TLC analysis for 1 h. The resulted
17. Ollevier, T.; Li, Z. Y. Eur. J. Org. Chem. 2007, 5665.
18. Lingaiah, B. V.; Ezikiel, G.; Yakaiah, T.; Reddy, G. V.; Rao, P. S. Tetrahedron Lett.
2006, 47, 4315.
19. (a) Jiang, N.; Hu, Q.; Reid, C. S.; Lu, Y.; Li, C. J. Chem. Commun. 2003, 2318; (b)
Zhao, H.; Cai, M. Z. Chin. J. Chem. 2006, 24, 1669.
solution was subject to evaporation and the residue was dissolved in Et
20 mL). The catalyst was precipitated and was filtered out, and could be
immediately reused in the next reaction. The organic layer was mixed with
methanol and 2 N HCl (1 mL) and stirred for 15 min, and then NaHCO (10%)
2
O
(
3